40015-25-6Relevant articles and documents
Aniline-initiated and Br?nsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR
Chen, De,Cheng, Chaozhihui,Deng, Wei,Guan, Wenjian,Liu, Yuxuan,Luo, Yongyue,Xiang, Jiannan,Zhang, Jiajia
, (2020/12/01)
A highly novel method of direct synthesis of 2-aryl-3-sulfenylindoles in moderate to good yields was developed via one-pot tandem reaction of readily available α-aminocarbonyl compounds and catalytic amount of benzenamines with RSSR.
Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source
Liu, Changqing,Fan, Jian,Wu, Manyi,Chen, Jiahui,Zhao, Yiming,Xie, Meihua
, p. 819 - 825 (2018/07/30)
An iodine-PPh3 mediated sulfenylation of indoles in water with stable and odorless sodium sulfinates as the sulfur source is described. The reaction could afford monosulfenylated indoles in moderate to excellent yields under metal free conditions. Moreover, double C—H sulfenylation of indoles at 2- and 3-positions has also been achieved by using excess sodium sulfinates under the optimized reaction conditions.
Metal-free synthesis of 3-sulfenylindoles via an iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides
Tao, Li-Ming,Liu, Wen-Qi,Zhou, Yun,Li, Ai-Tao
, p. 644 - 646 (2013/02/22)
An efficient and metal-free method was developed to synthesise 3-sulfenylindoles via the iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides. In the presence of I2, various 3-sulfenylindoles were obtained in moderate
A flexible synthesis of indoles from ortho -substituted anilines: A direct synthesis of isocryptolepine
Kraus, George A.,Guo, Haitao,Kumar, Ganesh,Pollock Iii, Gerald,Carruthers, Heather,Chaudhary, Divya,Beasley, Jonathan
experimental part, p. 1386 - 1393 (2010/07/16)
The reaction of anilines bearing a benzylic activating group in the ortho position with aromatic aldehydes or α,β-unsaturated aldehydes results in an efficient synthetic route to substituted indoles. Georg Thieme Verlag Stuttgart · New York.
Palladium-catalyzed annulation of 2-(1-Alkynyl)benzenamines with disulfides: Synthesis of 3-sulfenylindoles
Guo, Yan-Jin,Tang, Ri-Yuan,Li, Jin-Heng,Zhong, Ping,Zhang, Xing-Guo
supporting information; experimental part, p. 2615 - 2618 (2009/12/29)
3-Sulfenylindoles can be efficiently prepared in moderate to good yields from 2-(1-alkynyl)benzenamines and disulfides using the palladium/air catalytic systems. The study also provides a useful route to the synthesis of fipronil analogues.
Synthesis of methylthio-substituted heterocycles using the complex of trifluoromethanesulfonic anhydride with dimethyl sulfide
Shevchenko,Karpov,Zakurdaev,Nenajdenko,Balenkova
, p. 137 - 143 (2007/10/03)
A new method was developed for the electrophilic introduction of methylthio group into a series of aromatic heterocyclic compounds through the hetaryl(dimethyl)sulfonium salts formed in the course of the reaction of the respective heterocycles with the complex of dimethyl sulfide and trifluoromethanesulfonic anhydride. By demethylation with triethylamine it was possible to obtain the methylthio-substituted heterocycles.
Indole-3-sulfonium Ylides and Related Sulfonium Salts. Chemical and Physical Properties
Park, Kyong-Hwi,Daves, G. Doyle
, p. 780 - 785 (2007/10/02)
Acid-base titration of the sulfonium salt-sulfonium ylide pair dimethyl(1H-indol-3-yl)sulfonium 3-(dimethylsulfonio)indolide, the corresponding 2-methyl or 2-phenyl analogues, or the homologous 3-diethylsulfonium compounds resulted, in each case, in a hysteresis; i.e., titration of the sulfonium ylide with acid gave a different set of pH values from those observed upon titration of the sulfonium salt with base.In related studies comparison of ultraviolet spectra of the sulfonium salts and ylides in anhydrous dioxane and in water revealed significant differences. 1H-NMR spectra of sulfonium salts in aqueous or aqueous trifluoroacetic acid solutions revealed the formation of a new species which (a) exhibited an acid-base titration hysteresis indistinguishable from that of the precursor salt, (b) exhibited ions in the mass spectra corresponding to a sulfonium salt plus a molecule of water, and (c) reverted to the precursor salt upon attempted purification.These results are consistent with covalent hydration across the highly polarized C-2, C-3 double bond of the indole ring.
Synthesis of indoles from anilines and intermediates therein
-
, (2008/06/13)
Preparing indoles and intermediates therefor by reacting an N-haloaniline with a β-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the β-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an α-ethyl-β -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like.
